[Journal logo]

Volume 69 
Part 1 
Page o138  
January 2013  

Received 10 November 2012
Accepted 18 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.050
wR = 0.177
Data-to-parameter ratio = 11.8
Details
Open access

4-Cyano-N-ethylspiro[chromene-2,4'-piperidine]-1'-carboxamide

aDepartment of Physics, Thiagarajar College, Madurai 625 009, India
Correspondence e-mail: vasan692000@yahoo.co.in

The title compound, C17H19N3O2, crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules, the pyran ring has a twisted conformation (5S4), with Q = 0.301 (3) Å, [theta] = 116.7 (6) and [varphi]= 213.6 (7)° for molecule A, and Q = 0.364 (2) Å, [theta] = 113.7 (3) and [varphi] = 213.0 (4)° for molecule B. In molecule B, the terminal ethyl group is disordered over two orientations with an occupancy ratio of 0.55 (1):0.45 (1). In the crystal, molecules A and B form very similar but separate R12(7) motifs through N-H...O and C-H...O hydrogen bonds. The resulting chains along [001] are interlinked by weaker C-H...O and C-H...[pi] interactions, forming layers parallel to the bc plane.

Related literature

For related structures, see: Rajalakshmi et al. (2012[Rajalakshmi, P., Srinivasan, N. & Krishnakumar, R. V. (2012). Acta Cryst. E68, o2732.]). For their biological activity, see: Kemnitzer et al. (2004[Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Wang, Y. & Zhao, J. (2004). J. Med. Chem. 47, 6299-6310.]); Mahdavi et al. (2011[Mahdavi, M., Davoodi, J., Zali, M. R. & Foroumadi, A. (2011). Biomed. Pharm. 65, 175-182.]); Patil et al. (2012[Patil, D. U., Nikum, P. A., Nagle, S. P. & Mahulikar, P. P. (2012). J. Pharm. Res. 5, 1383-1386.]); Vosooghi et al. (2010[Vosooghi, M., Rajabalian, S., Sorkhi, M., Badinloo, M., Nakhjiri, M., Negahbani, A. S., Asadipour, A., Mahdavi, M., Shafiee, A. & Foroumadi, A. (2010). J. Res. Pharm. Sci. 5, 9-14.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N3O2

  • Mr = 297.35

  • Monoclinic, P 21 /c

  • a = 22.7845 (8) Å

  • b = 14.3370 (5) Å

  • c = 9.8442 (3) Å

  • [beta] = 90.783 (1)°

  • V = 3215.42 (19) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 298 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.972, Tmax = 0.980

  • 26353 measured reflections

  • 5377 independent reflections

  • 3664 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.177

  • S = 1.04

  • 5377 reflections

  • 455 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4B-C9B benzene ring

D-H...A D-H H...A D...A D-H...A
N3A-H1N3...O2Ai 0.81 (3) 2.12 (3) 2.915 (3) 170 (3)
N3B-H2N3...O2Bii 0.83 (2) 2.19 (3) 2.983 (3) 160 (2)
C11A-H11B...O2Ai 1.00 (3) 2.27 (3) 3.246 (3) 165 (2)
C11B-H11C...O2Bii 0.95 (3) 2.50 (3) 3.344 (3) 147 (2)
C9B-H9B...O2Biii 0.92 (3) 2.58 (3) 3.473 (3) 163 (2)
C13A-H13B...Cg1iv 0.97 2.91 3.843 (3) 163
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+2, -y+1, -z+2; (iv) [x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLUTON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2085 ).


Acknowledgements

The authors thank the SAIF, IIT, Madras, India, for the X-ray intensity data collection facility.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Wang, Y. & Zhao, J. (2004). J. Med. Chem. 47, 6299-6310.  [CrossRef] [PubMed] [ChemPort]
Mahdavi, M., Davoodi, J., Zali, M. R. & Foroumadi, A. (2011). Biomed. Pharm. 65, 175-182.  [CrossRef] [ChemPort]
Patil, D. U., Nikum, P. A., Nagle, S. P. & Mahulikar, P. P. (2012). J. Pharm. Res. 5, 1383-1386.  [ChemPort]
Rajalakshmi, P., Srinivasan, N. & Krishnakumar, R. V. (2012). Acta Cryst. E68, o2732.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vosooghi, M., Rajabalian, S., Sorkhi, M., Badinloo, M., Nakhjiri, M., Negahbani, A. S., Asadipour, A., Mahdavi, M., Shafiee, A. & Foroumadi, A. (2010). J. Res. Pharm. Sci. 5, 9-14.  [ChemPort]


Acta Cryst (2013). E69, o138  [ doi:10.1107/S1600536812051124 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.